The bicorannulenyl dianion: A charged overcrowded ethylene

David Eisenberg, Edward A. Jackson, Jennifer M. Quimby, Lawrence T. Scott, Roy Shenhar*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Super bowl: Bicorannulenyl, a large biaryl composed of two corannulene bowls, effectively becomes an overcrowded ethylene upon reduction to form a dianion (see picture). DFT calculations and NMR spectroscopic experiments reveal the double-bond character of the connection between the two bowls. Three stable diastereomers that interconvert through bowl inversions and central bond rotations were shown to exist.

Original languageAmerican English
Pages (from-to)7538-7542
Number of pages5
JournalAngewandte Chemie - International Edition
Volume49
Issue number41
DOIs
StatePublished - 4 Oct 2010

Keywords

  • Annulenes
  • Carbanions
  • Conformation analysis
  • Conjugation
  • Overcrowded ethylenes

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